Urea derivatives



United States Patent UREA DERIVATIVES Paul J. Stolfel, St. Louis, and David J. Beaver, Richmond Heights, Mo., assignors to Monsanto Chemical Company, St. Louis, Mo., a corporation of Delaware No Drawing. Application October 29, 1956,

Serial No. 618,718

5 Claims. (Cl. 260-553) N-'( 3 ,4-dichlorophenyl) butenyl) urea N-( 3,4-dibromophenyl) butenyl) urea N-(3,5-dichl0rophenyl) butenyl) urea N'( 3,5 -dibromophenyl) butenyl) urea N-(3,4,5-trichlorophenyl) N'-cyclohexyl N'-(3-chloro- Z-butenyl) urea N-(3,4,5-tribromophenyl) N'-cyclohexyl N'-(3-ch1oro- Z-butenyl) urea N'-cyclohexyl N'-(3-chloro-2- N-cyclohexyl N'-(3-chloro-2- As illustrative of the preparation of the urea derivatives of this invention is the following:

Example I To a suitable reaction vessel equipped with an,

agitator is added and mixed approximately 9.4 parts by weight of 3,4-dichlorophenylisocyanate, approximately 9.4 parts by weight of N-(3-chloro-2-butenyl) cyclohexylamine, and approximately 36 parts by weight of diethyl ether. The mass is slowly agitated for about one hour at room temperature, filtered, and the filter cake washed with two 18 parts by weight portions of diethyl ether, and then air dried. The white solid product (approximately 17.5 parts by weight) is N-(3,4-dichlorophenyl) N'-cyclohexyl N'-(3-chloro-2-butenyl) urea, M. P. 160.4-160.8 C.

Example II Employing the procedure of Example I but employing instead of 3,4-dichlorophenylisocyanate an equal weight of 3,5-dichlorophenylisocyanate there is obtained N-(3,5-dichlorophenyl) N-cyclohexyl N-(3-chloro-2- butenyl) urea.

Example III Employing the procedure of Example I but replacing 3,4-dichlorophenylisocyanate with a chemically equivalent weight of 3,4,S-trichlorophenylisocyanate there is obtained N-(3,4,5-trichlorophenyl) N'-cyclohexyl N'-(3-chloro-2-butenyl) urea.

Example IV Employing the procedure of Example I but replac- ICC 2 ing 3,4-dichlorophenylisocyanate with a chemically equivalent weight of 3,4-dibromophenylisocyanate there is obtained N-(3,4-dibromopheny1) N-cyclohexyl N,- (3-chloro-2-butenyl) urea.

In the preparation of the new compounds of this invention other inert solvents than diethyl ether may be employed, e. g. di-isopropyl ether, methylbutyl ether, the liquid alkanes and the like. The reaction temperature employed in preparing the new compounds will depend upon the particular reactants and in general will be between room temperature and the reflux temperature of the system.

The compounds of this invention are particularly useful in controlling bacterial growth, particularly Micro coccus pyogenes vanaureus. In this regard the urea derivatives of this invention when compounded with a detergent soap (i. e. an alkali metal salt of a higher fatty acid of animal or vegetable origin, such as stearic acid, lauric acid, palmitic acid, oleic acid, linoleic acid, ricinoleic acid, and the like, or mixtures thereof obtained from tallow, lard, cocoanut oil, palm oil, castor oil, olive oil, cottonseed oil, and the like) provide highly useful antiseptic detergent soap compositions.

In order to illustrate the activity of the urea derivatives of this invention N-(3,4-dichlorophenyl) N-cyclohexyl N'-(3-chloro-2-butenyl) urea was incorporated in an alkali metal fatty acid soap, a mixture of sodium and potassium salts of fatty acids whose fatty acid content analyzes Percent Oleic and linoleic acid About 46 Stearic acid About 14 Palmitic acid About 30 Lower fatty acids (myristic, lauric, etc.) About 10 in a weight ratio of one part to 50 parts soap. Aliquots were added to a Sabourards dextrose agar medium so 'as to give concentrations in parts per million as set forth below. The agar in each case was then poured into a petri dish, allowed to harden and then inoculated with a standard culture of Micrococcus pyogenes var. aureus of standard resistance. The incubation in each instance was made at 37 C. for 48 hours. The extent of growth is noted below:

Compound/Concentration, p. p. m 1,000 i 100 l 10 N-(3,4-dichlorophenyl) N-cyclohexyl N- (3-chloro-2-butenyl) urea none none none eifective antiseptic detergent soap compositions. Amounts as low as 0.5 to 1% by weight based on the weight of the detergent soap have proved satisfactory. However, it is preferred to employ these urea derivatives in amounts in the order of 1 to 5% by weight based on the detergent soap. While larger amounts, as for example up to 10% by weight, may be employed the upper limit will be determined by practical considerations. Various colors, antioxidants, perfumes, water softeners, emollients, and the like, may be included where desirable in detergent compositions containing the urea derivatives of this invention. The term soap or detergent soap as used and a fat or fattyacid, both saturated andunsaturated.

W'nile this invention has been described with respect to certain embodiments it is not so limited and it is to be imderstood that variations and modifications thereof obvious to those skilled in the art may be made without departing from the'spirit or scope of this invention.

What is claimed is: 1. Compounds of the structure V cyclohexyl XflCaHs-,.NHO-N CHzCH=OClOHa wherein Xnc6H5n is a halogen substituted phenyl radical free ofsubstituents ortho to the nitrogen atom, where X is a halogen atom and where n is a whole number from 2 to 3.

"2,803,655 a w a 2. Compounds of claim 1 wherein X is selected from the group" consisting of chlorine and bromine.

3. Compounds of claim 1 wherein X is chlorine and where n is two.

4. N-(3,4-dichlorophenyl) N'-cyclohexyl N-(3-chloro-2-butenyl) urea.

5. The process of making the compounds of claim 1 which comprises reacting in substantially equimolecular proportions N-(3-chloro-2-butenyl) cyclohexylamine and an isocyanate of the structure XnC6H5nNcO,

wherein XnC6H5-n, X and n have the same significance as in claim 1, in an inert organic solvent at a temperature in the range of room temperature to the reflux temperature of the system.

No references cited. 

1. COMPOUNDS OF THE STRUCTURE 